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Cruise Dates

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October 2026

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Silver Shadow

Silversea

Feb 6, 2027 - Feb 16, 2027 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Little Bay, Montserrat • Les Saintes, F.W.I. • Roseau, Dominica • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados

Average Starting Price

$4,450pp

Jim's Onboard Credit

29% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 20, 2027 - Mar 30, 2027 (10 Nights)

Miami • St. Thomas • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • St John's, Antigua • Tortola • San Juan, Puerto Rico

Average Starting Price

Jan 13, 2027 - Jan 29, 2027 (16 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 7, 2027 - Dec 17, 2027 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

Nov 6, 2027 - Nov 21, 2027 (15 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

Jan 6, 2028 - Feb 19, 2028 (44 Nights)

Los Angeles • Ensenada • Cabo San Lucas • Acapulco, Mexico • Puerto Quetzal, Guatemala • Puntarenas, Costa Rica • Panama Canal, Panama • Cartagena, Colombia • George Town, Cayman Islands • Miami • Philipsburg, St. Maarten • Fort-De-France, Martinique • Castries, St. Lucia • Grenada • Oranjestad, Aruba • Miami • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • Cruising the Straits of Florida • Cozumel • Roatan, Honduras • Harvest Caye, Belize • Costa Maya • Cruising the Straits of Florida • Miami

Average Starting Price

Oct 16, 2027 - Oct 23, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 9, 2027 - Dec 19, 2027 (10 Nights)

Average Starting Price

Nov 29, 2026 - Dec 20, 2026 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,164pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

18% OFF

Seven Seas Mariner

Regent Seven Seas Cruises

Jan 4, 2027 - Jan 22, 2027 (18 Nights)

Miami • St. Thomas • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Devil's Island, France • Atlantic Ocean cruising • Fortaleza, Brazil • Recife, Brazil • Maceio, Brazil • Salvador, Brazil • Buzios, Brazil • Rio de Janeiro, Brazil

Average Starting Price

9% OFF

Dec 22, 2028 - Jan 3, 2029 (12 Nights)

Fort Lauderdale • Grand Turk • St John's, Antigua • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • St. Kitts • Fort Lauderdale

Average Starting Price

$8,350pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Insignia

Oceania Cruises

Nov 24, 2026 - Dec 19, 2026 (25 Nights)

Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Cruising the Amazon River • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico • Nassau • Miami

Average Starting Price

$13,249pp

Jim's Onboard Credit

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